KR910009684A - 방향족 아민 화합물, 이의 제조방법 및 이들의 존재하는 약제학적 조성물 - Google Patents

방향족 아민 화합물, 이의 제조방법 및 이들의 존재하는 약제학적 조성물 Download PDF

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KR910009684A
KR910009684A KR1019900017897A KR900017897A KR910009684A KR 910009684 A KR910009684 A KR 910009684A KR 1019900017897 A KR1019900017897 A KR 1019900017897A KR 900017897 A KR900017897 A KR 900017897A KR 910009684 A KR910009684 A KR 910009684A
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South Korea
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group
formula
compound
benzylpiperidin
hydrogen
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KR1019900017897A
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English (en)
Inventor
에몽잘 그자비에
굴라우이크 삐에르
프로이에또 빈센쬬
반 브뢰크 디디에
Original Assignee
미쉘드 아스
소시에떼 아노님 사노피
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Priority claimed from FR8914517A external-priority patent/FR2654100B1/fr
Priority claimed from FR9007534A external-priority patent/FR2663329B1/fr
Application filed by 미쉘드 아스, 소시에떼 아노님 사노피 filed Critical 미쉘드 아스
Publication of KR910009684A publication Critical patent/KR910009684A/ko

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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
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    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
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    • A61P25/00—Drugs for disorders of the nervous system
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    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
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    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • C07D211/28—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms to which a second hetero atom is attached
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    • C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
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Abstract

내용 없음

Description

방향족 아민 화합물, 이의 제조방법 및 이들이 존재하는 약제학적 조성물
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Claims (23)

  1. 일반식(Ⅰ)의 화합물 또는 이의 무기산 또는 유기산과의 염.
    상기식에서, m은 1∼3의 정수이고;Ar 및 Ar′는 각각 티에닐기;치환되지 않은 페닐기이거나 할로겐원자,C1-C3알킬, 트리플로오로메틸, 알콕시(여기서, 알킬은 C1-C3이다);히드록실 또는 메틸렌디옥시기에 의해 일- 또는 이치환된 페닐기; 또는 이미다졸릴기이며, Ar′은 치환되지 않았거나 할로겐에 의해 치환된 벤조티에닐기;치환되지 않았거나 할로겐에 의해 치환된 나프틸기;비페닐기;또는 치환 되지 않았거나 질소에 벤질기가 치환된 인돌릴기일 수 있으며-X는 수소이고-X′는 수소 또는 히드록실기이거나 하기의 X′와 결합하여 탄소-탄소 결합을 형성하며, 또는 X및X′가 함께 옥소기 또는 =N-O(CH2)P-Am의기(식에서, P는 2또는 3이며 Am은 디알킬아미노기이다)의 디알킬아미노알콕시아미노기를 형성하며, 각 알킬기는 탄소수가 1 내지 4일수 있고-Y는 질소원자 또는 C(X″)기(식에서, X″는 수소원자이거나 X′와 탄소-탄소 결합을 형성한다)이며-Q는 수소원자, C1-C4알킬기 또는 -(CH2)q-Am′의기(식에서, q는 2 또는 3이고 Am′은 피페리디노, 4-벤질과 페리디노 또는 디알킬아미노기이다)의 아미노알킬이고, 각 알킬기는 탄소수가 1 내지 4일수 있으며;R은 수소, 메틸기 또는 (CH2)n-L의기(식에서, n은 2∼6의 정수이고 L은 수소 또는 아미노기이다)이고;-T는및(식에서, W는 산소 또는 황원자 이다)로부터 선택된 기이며;-Z는 수소원자이거나, 혹은 T가 -C(=O)-의 기이면 M이거나 OM이며, 또는 T가 -C(=W)-NH-의 기이면 M이고, 여기에서, M은 수소;직쇄 또는 축쇄의 C1-C6알킬;치환되지 않은 페닐알킬기이거나 방향족 고리상에 할로겐, 히드록실, 탄소수 1 내지 4의 알콕시 또는 탄소수 1 내지 4의 알킬기로 일-또는 다치환된, 알킬기와 탄소수가 1 내지 3인 페닐알킬;알킬기의 탄소수가 1 내지 3인 피리딜알킬;알킬기의 탄소수가 1 내지 3인 나프틸알킬;알킬기의 탄소수가 1 내지 3인 피리딜티오알킬;스티릴;알킬기의 탄소수가 1 내지 3인 1-메틸아미다졸-2-일티오알킬;1-옥소페닐-3-인단-2-일;또는 치환되지 않았거나 일-또는 다치환된 방향족기 혹은 헤테로 방향족기이다.
  2. 일반식(Ⅰ*)의 광학적으로 순수한 화합물 또는 이의 무기산 또는 유기산과의 염.
    상기식에서, -n*n-n*n는 이 기호로 표시된 탄소원자가 제한된(+) 또는 (-)절대 배열을 가짐을 의미하며;-m,Ar,X,x′,Y,Q,R,T 및 M은 제1항에서 정의 한 바와 같다.
  3. N-[4-(4-벤질피페리딘-1-일)-2-(3,4-디클로로페닐)부틸]-2,4-디클로로벤즈 아미드 또는 이의 약제학적 허용가능염.
  4. N-[4-(4-벤질피페리딘-1-일)-2-(3,4-디플루오로페닐)부틸]-2,4-디클로로벤즈 아미드 또는 이의 약제학적 허용가능염.
  5. N-[4-(4-벤질피페리딘-1-일)-2-(3,4-디클로로페닐)부틸]-4-플루오로나프탈렌-1-카르복스아미드 또는 이의 약제학적 허용가능염.
  6. N-[4-(4-벤질피페리딘-1-일)-2-(3,4-디플루오로페닐)부틸]-2,4-디클로로벤즈 아미드(+) 또는 이의 약제학적 허용가능염.
  7. N-[4-(4-벤질피페리딘-1-일)-2-(3,4-미클로로페닐)부틸]-2,4-디클로로벤즈 아미드(-) 또는 이의 약제학적 허용가능염.
  8. N-[4-(4-벤질피페리딘-1-일)-2-(3,4-디플루오로페닐)부틸]-2,4-디클로로벤즈 아미드(+) 또는 이의 약제학적 허용가능염.
  9. N-[4-(4-벤질피페리딘-1-일)-2-(3,4-디플로오로페닐)부틸]-2,4-디클로로벤즈 아미드(-) 또는 이의 약제학적 허용가능염.
  10. N-[4-(4-벤질피페리딘-1-일)-2-(3,4-미클로로페닐)부틸]-4-플루오로나프탈렌-1-카르복스아미드(+) 또는 이의 약제학적 허용가능염.
  11. N-[4-(4-벤질피페리딘-1-일)-2-(3,4-디클로로페닐)부틸]-4-플루오로나프탈렌-1-카르복스아미드(-) 또는 이의 약제학적 허용가능염.
  12. a)일반식(Ⅲ)의 유리 아민을 일반식(Ⅲ)의 산 작용성 유도체(T가 -CO-인, 일반식(Ⅰ)의 화합물을 제조하고자 하는 것이다) 또는 일반식(Ⅲ′)의 이소(티오)시아네이트(T가-C(W)-NH-인, 일반식(Ⅰ)의 화합물을 제조하고자 하는 것이다)로 처리하여 일반식(Ⅳ)의 화합물을 형성시키고,
    [상기식에서 m,Ar′ 및 Q는 제1항에서 정의한 바와 같고;R0는 수소, 메틸기 또는 (CH2)n-L0의기(식에서, n은 제1항에서 정의한 바와 같고 L0은 수소원자 또는 N-보호기에 의해 보호된 아미노기이다)이며;E는 히드록실기, 테트라이히드로피틴-2-일옥시기와 같은 O-보호기, 또는
    의 기(식에서, Ar,X 및 Y는 제1항에서 정의한 바와 같고 X0는 제1항의 X′기와 같으며, 여기에서 히드록실기는 0-보호기에 의해 보호된것)이다]
    HO-CO-Z (Ⅲ)
    (상기식에서, Z는 제1항에서 정의한 바와같다)
    W=C=N-Z (Ⅲ′)
    (상기식에서, W와 Z는 제1항에서 정의한 바와같다)
    (Ⅳ)
    b)E가 테트라이히드로피라닐옥시면, 단계,a)에서 일반식(Ⅱ)의 출발 아민상에서 선택적으로 수행하는 산 가수분해에 의해 테트라히드로피라닐기를 제거하고, (c)생성된 일반식 (Ⅴ)의 N-치환 알칸을아민을 메탄솔포닐 클로라이드로 처리하고,
    (Ⅴ)
    d)생성된 일반식(Ⅵ)의 메실레이트를 일반식(Ⅶ)의 아치 아민과 반응시키고,
    (Ⅵ)
    (Ⅶ)
    (상기식에서, Ar,Y,X 및 X′는 제1항에서 정의한 바와 같다)
    e)존재하는 특정한 O-보호기와 N-보호기를 제거하고, 적당하다면, 생성물을 그의 염으로 전환시킴을 특징으로 하는, 제1항의 화합물의 제조방법.
  13. 일반식(ⅩⅤⅠⅠ*)의 화합물을 산매질내, 용매내에서 처리하여, 산매질 내에서, 알칸올 AIKOH(여기에서, AIK는 탄소수 1내지 4의 알킬기이다)내에서 에스테르화되는 일반식(ⅩⅤⅠⅠ*)의 아미노산을 수득한 다음;
    상응하는 일반식(ⅩⅤⅠⅠ*)의 에스테르를 일반식(Ⅲ)의 산 작용성 유도체를 또는 일반식(Ⅲ′)의 이소(티오)시아네이트로 처리하고;
    (상기식에서, AIK는 상기에서 정의한 바와같고, Q,Ar′및 m은 제1항에서 정의한 바와 같으며 R0는 제12항에서 정의한 바와 같다)
    HO-CO-Z (Ⅲ)
    W=C=N-Z (Ⅲ′)
    (상기식에서, Z및 W는 제2항에서 정의한 바와같다)생성된 일반식(XX*)의 에스테르에 환원제를 작용시키고;
    (XX*)
    일반식(V*)의 상응 알콜을 일반식(Ⅵ*)의 메탄술포네이트에 스테르(이는 일반식(Ⅶ)의 아민으로 처리하고, 적당하다면 탑보호시켜 적당하다면 그의 염으로 전환되는 일반식(Ⅰ*)의 화합물이 얻어진다)로 전환시킴을 특징으로 하는 제2항의 광학적으로 순수한 일반식(Ⅰ*)의 화합물의 입체 선택적 제조방법.
    (상기식에서, Ar,x,x′및 Y는 제1항에서 정의한 바와 같다)
  14. 일반식(XVI)의 화합물 또는 그의 염.
    상기식에서, Enn은 테트라히드로피라닐옥시기 히드록실기 또는
    의기이고;
    -X0는 수소원자 또는 유리되어 있거나 O-보호기로 보호되어 있는 히드록실기이거나, 하기의 X″와 결합하여 탄소-탄소 결합을 형성하며, 또는 X와 X0가 함께 옥소기 또는 일반식=N-O-(CH2)-Am(식에서, P는 2 또는 3이고, Am은 디알킬아미노기이다)의 디알킬아미노알콕시이미노기를 형성하며, 각 알킬기는 탄소수 1내지 4일수 있고-Y는 질소원자 또는 C(X″)의 기(식에서, X″는 수소원자이거나 X0와 탄소-탄소 결합을 형성한다)이며;-R0는 수소, 메틸기 또는 (CH2)n-L0기(식에서, n은 2∼6이며 L0는 수소원자 또는 유리되어 있거나 N-보호기로 보호되어 있는 아미노기이다)이고;m,Ar,Ar′,X 및 Q는 제1항에서 정의한 바와 같다.
  15. 제14항에 있어서, 광학적으로 순수한 일반식(XVI)의 화합물의 m,Q 및 Ar′가 제1항에서 정의한 바와 같고 E0가 히드록실기이며 R0가 제12항에서 정의한 바와 같은 R0인 화합물.
  16. 일반식(V′)의 화합물 또는 이의 염.
    상기식에서, G는 수소원자, 테트라히드로피라닐기 또는 메탄술포닐기며;R0는 수소원자, 메틸기 또는 (CH2)n-L0의 기(식에서, n은 2∼6이고 L0는 수소원자 또는 유리되어 있거나 N-보호기로 보호되어 있는 아미노기이다)이고;m,Ar,Ar′,X 및 Q는 제1항에서 정의한 바와 같다.
  17. 제16항에 있어서, 광학적으로 순수한 일반식(V′)의 화합물의 m,Q,T,Ar′ 및 Z가 1항에서 정의한 바와 같으며 G가 수소원자이고 R0가 제12항에서 정의한 바와 같은 R0인 화합물.
  18. 제16항에 있어서, 광학적으로 순수한 일반식(V′)의 화합물의 m,Q,T,Ar′ 및 Z가 1항에서 정의한 바와 같으며 G가 메탄술포닐기이고 R0가 제12항에서 정의한 바와 같은 R0인 화합물.
  19. 활성 성분으로 제1항 또는 제2항에 따른 일반식(I) 또는 (I*)의 화합물을 함유하는 약제학적 조성물.
  20. 제19항에 있어서, 활성 성분을 한가지 이상의 약제학적 부형제와 혼합하여 투여단위 형태로 만들어진 약제학적 조성물.
  21. 제20항에 있어서, 활성 성분을 2.5내지 1000㎎ 함유하는 약제학적 조성물.
  22. 제14항에 있어서, E00가 히드록실기이고 R00가 수소원자인 화합물.
  23. N-메틸-N[4-(4-벤질피페리딘-1-일)-2-(3,4-디클로로페닐)부틸]페닐 아세트 아미드.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900017897A 1989-11-06 1990-11-06 방향족 아민 화합물, 이의 제조방법 및 이들의 존재하는 약제학적 조성물 KR910009684A (ko)

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FR8914517A FR2654100B1 (fr) 1989-11-06 1989-11-06 Arylalkylenediamines, procede pour leur preparation et compositions pharmaceutiques les contenant.
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FR9007534A FR2663329B1 (fr) 1990-06-15 1990-06-15 Composes aromatiques amines, procede pour leur preparation et compositions pharmaceutiques les contenant.

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LV10713A (lv) 1995-06-20
US5618938A (en) 1997-04-08
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AU6583890A (en) 1991-05-23
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NO904802L (no) 1991-05-07
EP0428434A3 (en) 1991-10-09
HU913346D0 (en) 1992-01-28
AU649973B2 (en) 1994-06-09
HUT56543A (en) 1991-09-30
PL165758B1 (pl) 1995-02-28
NO904802D0 (no) 1990-11-05
FI97540C (fi) 1997-01-10
NZ235985A (en) 1993-10-26
US5686609A (en) 1997-11-11
IL96241A (en) 1996-03-31
AU5924594A (en) 1994-06-02
PT95790A (pt) 1991-09-13
CA2029275A1 (en) 1991-05-07
EP0428434A2 (fr) 1991-05-22
US5317020A (en) 1994-05-31
NO177299C (no) 1995-08-23
NO177299B (no) 1995-05-15
PL166565B1 (pl) 1995-06-30
PL293823A1 (en) 1993-01-25
IL96241A0 (en) 1991-08-16

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